Sodium Bicarbonate → HCID 63320628, compound

HRID 2040563Notes

Reaction equation

HRID 2040563 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([C:10](O)=[O:11])=[CH:8][C:7]=2[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+]>C1COCC1>[CH:1]1([CH2:4][O:5][C:6]2[CH:14]=[CH:13][C:9]([CH2:10][OH:11])=[CH:8][C:7]=2[C:15]([F:16])([F:17])[F:18])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 63320442HCID 63320442, compound

Product 1

HCID 63320628HCID 63320628, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(cyclopropylmethoxy)-3-(trifluoromethyl)benzoic acid in THF (7 mL) at 0° C. was slowly added BH3DMS (2.0 M in THF) (1.592 mL, 3.18 mmol). After stirring for 0.5 h at 0° C., the reaction was allowed to return to room temperature and stirred overnight. The reaction mixture was slowly added to a saturated solution of NaHCO3 at 0° C. and extracted with EtOAc (thrice). The combined extracts were dried over MgSO4 and purified by silica gel column chromatography to give the title compound as a solid (0.358 g). 1H NMR (400 MHz, CDCl3) δ ppm 0.34-0.43 (m, 2H), 0.57-0.67 (m, 2H), 1.22-1.32 (m, 1H), 3.94 (d, J=6.57 Hz, 2H), 4.66 (s, 2H), 6.96 (d, J=8.46 Hz, 1H), 7.46 (dd, J=8.46, 2.02 Hz, 1H), 7.57 (s, 1H).

Workup

  1. customat 0° C.
  2. customto return to room temperature
  3. stirringstirred overnight
  4. extractionextracted with EtOAc (thrice)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-c287aae1860f4e68a1a995872b210ff7
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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